JPS60124659A - 反応染料の製造方法 - Google Patents
反応染料の製造方法Info
- Publication number
- JPS60124659A JPS60124659A JP59236011A JP23601184A JPS60124659A JP S60124659 A JPS60124659 A JP S60124659A JP 59236011 A JP59236011 A JP 59236011A JP 23601184 A JP23601184 A JP 23601184A JP S60124659 A JPS60124659 A JP S60124659A
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- dye
- cyanuric chloride
- carried out
- dyes
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 239000000985 reactive dye Substances 0.000 title claims description 5
- 239000000975 dye Substances 0.000 claims description 48
- 238000006243 chemical reaction Methods 0.000 claims description 42
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 35
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 32
- 150000001412 amines Chemical class 0.000 claims description 22
- 125000003277 amino group Chemical group 0.000 claims description 21
- 239000000987 azo dye Substances 0.000 claims description 19
- 229910021529 ammonia Inorganic materials 0.000 claims description 17
- 125000000129 anionic group Chemical group 0.000 claims description 14
- 239000007859 condensation product Substances 0.000 claims description 13
- 230000008878 coupling Effects 0.000 claims description 11
- 238000010168 coupling process Methods 0.000 claims description 11
- 238000005859 coupling reaction Methods 0.000 claims description 11
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 238000002955 isolation Methods 0.000 claims description 6
- 238000006193 diazotization reaction Methods 0.000 claims description 5
- -1 diazobutylene Chemical group 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 claims description 2
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims 2
- 241001024304 Mino Species 0.000 claims 1
- 239000001000 anthraquinone dye Substances 0.000 claims 1
- 238000010924 continuous production Methods 0.000 claims 1
- 239000001007 phthalocyanine dye Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- 239000000243 solution Substances 0.000 description 19
- 235000011121 sodium hydroxide Nutrition 0.000 description 10
- 238000003756 stirring Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 239000007900 aqueous suspension Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000001694 spray drying Methods 0.000 description 2
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
- ZNXSFVXZQBETRJ-UHFFFAOYSA-N (3-aminophenyl)urea Chemical compound NC(=O)NC1=CC=CC(N)=C1 ZNXSFVXZQBETRJ-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical class C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
- GFPQSWFFPRQEHH-UHFFFAOYSA-N 7-aminonaphthalene-1,3,6-trisulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(N)=CC2=C1S(O)(=O)=O GFPQSWFFPRQEHH-UHFFFAOYSA-N 0.000 description 1
- PQJUJGAVDBINPI-UHFFFAOYSA-N 9H-thioxanthene Chemical class C1=CC=C2CC3=CC=CC=C3SC2=C1 PQJUJGAVDBINPI-UHFFFAOYSA-N 0.000 description 1
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical class C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000005282 brightening Methods 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001791 phenazinyl group Chemical class C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- CJABVFCUCRAVOK-UHFFFAOYSA-N pyrene-1,2-dione Chemical class C1=C2C(=O)C(=O)C=C(C=C3)C2=C2C3=CC=CC2=C1 CJABVFCUCRAVOK-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 239000007974 sodium acetate buffer Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000004961 triphenylmethanes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH606983 | 1983-11-10 | ||
| CH6069/83-4 | 1983-11-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS60124659A true JPS60124659A (ja) | 1985-07-03 |
Family
ID=4303733
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59236011A Pending JPS60124659A (ja) | 1983-11-10 | 1984-11-10 | 反応染料の製造方法 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4785081A (de) |
| EP (1) | EP0145655B1 (de) |
| JP (1) | JPS60124659A (de) |
| DE (1) | DE3479589D1 (de) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE38023E1 (en) | 1995-07-24 | 2003-03-11 | L'oreal | Head for dispensing a liquid product in the form of an aerosol and dispenser equipped with such a head |
| US6824077B2 (en) | 2001-07-20 | 2004-11-30 | L'oreal | Dispenser head having two nozzles |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8619914D0 (en) * | 1986-08-15 | 1986-09-24 | Ici Plc | Reactive dyes |
| US5196033A (en) * | 1986-08-15 | 1993-03-23 | Imperial Chemical Industries Plc | BIS-azotriazinyl reactive dyes having an N-alkyl-phenylenediamine link for cellulose textiles |
| DK0437184T3 (da) * | 1990-01-09 | 1994-05-16 | Ciba Geigy Ag | Fremgangsmåde til trichromifarvning eller -trykning af celluloseholdige textilfibermaterialer |
| DE4137291A1 (de) * | 1991-11-13 | 1993-05-19 | Bayer Ag | Verfahren zur kontinuierlichen umsetzung von halogenpyrimidinen mit aminen |
| CN106833012B (zh) * | 2016-12-05 | 2018-08-31 | 泰兴锦云染料有限公司 | 一种活性黄染料及其制备和应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1386625A (en) * | 1972-06-14 | 1975-03-12 | Ici Ltd | Reactive disazo dyestuffs |
| DE3014662A1 (de) * | 1980-04-16 | 1981-10-22 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von wasserloeslichen phthalocyaninfarbstoffen |
| CH655735A5 (de) * | 1982-09-17 | 1986-05-15 | Sandoz Ag | Reaktive monoazoverbindungen. |
-
1984
- 1984-11-05 DE DE8484810536T patent/DE3479589D1/de not_active Expired
- 1984-11-05 EP EP84810536A patent/EP0145655B1/de not_active Expired
- 1984-11-10 JP JP59236011A patent/JPS60124659A/ja active Pending
-
1986
- 1986-09-22 US US06/912,175 patent/US4785081A/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE38023E1 (en) | 1995-07-24 | 2003-03-11 | L'oreal | Head for dispensing a liquid product in the form of an aerosol and dispenser equipped with such a head |
| US6824077B2 (en) | 2001-07-20 | 2004-11-30 | L'oreal | Dispenser head having two nozzles |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0145655A2 (de) | 1985-06-19 |
| EP0145655A3 (en) | 1986-11-26 |
| EP0145655B1 (de) | 1989-08-30 |
| DE3479589D1 (en) | 1989-10-05 |
| US4785081A (en) | 1988-11-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2560422C2 (de) | Reaktivfarbstoffe, deren Herstellung und Verwendung | |
| KR920001489B1 (ko) | 반응성 금속 포르마잔 화합물의 제조방법 | |
| KR870000785B1 (ko) | 시아누르산 플루오라이드와 아민의 연속반응 방법 | |
| JP2557855B2 (ja) | 水溶性アゾ化合物及び該化合物を染料として使用する方法 | |
| JPS60124659A (ja) | 反応染料の製造方法 | |
| US4189576A (en) | Process for monoacylating water-soluble organic amino compounds | |
| EP0014844B1 (de) | Fluortriazin-Derivate, Verfahren zur Herstellung von Fluortriazin-Derivaten und von Reaktivfarbstoffen und deren Verwendung | |
| JPS6165856A (ja) | α‐（ο‐クロルフエニル）‐アミノメチレン‐β‐ホルミルアミノプロピオニトリル及びその製法 | |
| JPH04227970A (ja) | 反応染料、その製造方法と使用方法 | |
| US3959342A (en) | Process for the preparation of nitrilotriacetonitrile (NTN) | |
| JPS6375067A (ja) | 反応染料とその製造方法と使用 | |
| JPH0317073A (ja) | 置換された２，４―ジアミノ―６―フルオローｓ―トリアジン類の製造方法 | |
| US7109313B2 (en) | Water-soluble reactive mono- and di-azo dyes | |
| US5440039A (en) | Process for the continuous reaction of cyanuric fluoride with amines and a reactor for carrying out this process | |
| JPH10513495A (ja) | 反応性アゾ染料の製造方法 | |
| US4376737A (en) | Process for the production of naphthylaminehydroxysulphonic acids | |
| US4361698A (en) | Process for the manufacture of dihalogenotriazinylamino-naphthol compounds | |
| JPH0368071B2 (de) | ||
| RU2076096C1 (ru) | Способ получения п-нитрозофенола | |
| EP0641838A1 (de) | Reaktivfarbstoffe auf Basis einer substituierten Barbitursäure | |
| US5332813A (en) | Process for the continuous reaction of difluorotriazinyl compounds with amines | |
| KR960014048B1 (ko) | 피리미딘계 반응성 염료의 제조방법 | |
| JP2557475B2 (ja) | トリフエンジオキサジンの製造方法 | |
| KR820000694B1 (ko) | S-트리아진계 반응성 염료의 제조방법 | |
| CN1102621C (zh) | 活性双偶氮染料 |